An ionophore with diverse biological activities
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Alborixin

Item No. 40933

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(αR,2S,3S,5R,6S)-6-[(2R,3S)-3-[(2R,5S,6R)-6-[[(2R,3S,5R,6R)-6-[(R)-[(2S,2′R,3′R,5S,5′S)-5′-[(2R,5R,6S)-6-ethyltetrahydro-5-hydroxy-5-methyl-2H-pyran-2-yl]octahydro-2′-hydroxy-2,3′,5′-trimethyl[2,2′-bifuran]-5-yl]hydroxymethyl]tetrahydro-6-hydroxy-3,5-dimethyl-2H-pyran-2-yl]methyl]tetrahydro-6-hydroxy-5-methyl-2H-pyran-2-yl]-2-hydroxybutyl]tetrahydro-α,3,5-trimethyl-2H-pyran-2-acetic acid
CAS Number
57760-36-8
Molecular Formula
C48H84O14
Formula Weight
885.2
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: SolubleDMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
O[C@@H]([C@H](C)[C@]1([H])O[C@@](C[C@H]2O[C@]([C@H](O)[C@]3([H])CC[C@]([C@@]4(O)[C@H](C)C[C@]([C@]5([H])O[C@@H](CC)[C@@](O)(C)CC5)(C)O4)(C)O3)(O)[C@H](C)C[C@@H]2C)(O)[C@@H](C)CC1)C[C@H]6[C@H](C)C[C@H](C)[C@]([C@@H](C)C(O)=O)([H])O6
InChi Code
InChI=1S/C48H84O14/c1-13-38-43(10,53)18-17-39(58-38)44(11)23-30(7)48(56,62-44)45(12)19-16-35(59-45)41(50)47(55)29(6)21-26(3)37(61-47)24-46(54)28(5)14-15-34(60-46)31(8)33(49)22-36-25(2)20-27(4)40(57-36)32(9)42(51)52/h25-41,49-50,53-56H,13-24H2,1-12H3,(H,51,52)/t25-,26+,27+,28+,29-,30-,31+,32-,33-,34-,35+,36+,37-,38+,39-,40+,41-,43-,44+,45+,46-,47-,48-/m1/s1
InChi Key
WWDHGOLBPBWCNJ-GXXSWWTOSA-N
Origin
Bacterium/Streptomyces lasii
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $131

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    Product Description

    Alborixin is an ionophore originally isolated from S. albus that has diverse biological activities.1,2,3,4 It is active against B. cereus, B. megaterium, S. lactis, S. aureus, and C. xerosis (MIC50s = 0.4, <0.1, 0.8, 0.2, 0.8 mg/kg, respectively).1 Alborixin decreases the proliferation of eight cancer cell lines (IC50s = 3.2 to 15.4 µM).2 It induces apoptosis, decreases the mitochondrial membrane potential, and increases the levels of reactive oxygen species (ROS) in HCT116 colon cancer cells when used at a concentration of 5 µM. Alborixin (1 mg/kg) increases heart rate, right ventricular contractile force, systolic and diastolic arterial blood pressure, and plasma levels of glucose in the coronary sinus and hepatic veins, as well as decreases the QT interval and plasma levels of potassium and sodium, but not calcium, in the coronary sinus and hepatic, renal, and deep femoral veins in normotensive dogs.3 It reduces the number of C. parvum oocytes in C. parvum-infected mice when administered at doses of 1.5 or 2.5 mg/kg.4 Alborixin is toxic to mice (LD50 = 150 mg/kg).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Delhomme, C., Kergomard, A., Kergomard, G., et al. Alborixin, a new antibiotic ionophore: Taxonomy, isolation and biological properties. J. Antibiot. (Tokyo) 29(7), 692-695 (1976).

    2. Shah, A.M., Wani, A., Qazi, P.H., et al. Isolation and characterization of alborixin from Streptomyces scabrisporus: A potent cytotoxic agent against human colon (HCT-116) cancer cells. Chem. Biol. Interact. 256, 198-208 (2016).

    3. Moins, N., Gachon, P., and Duchene-Marullaz, P. Effects of two monocarboxylic ionophores, grisorixin and alborixin, on cardiovascular function and plasma cation concentrations in the anesthetized dog. J. Cardiovasc. Pharmacol. 1(6), 659-671 (1979).

    4. Blagburn, B.L., Sundermann, C.A., Lindsay, D.S., et al. Inhibition of Cryptosporidium parvum in neonatal Hsd:(ICR)BR Swiss mice by polyether ionophores and aromatic amidines. Antimicrob. Agents Chemother. 35(7), 1520-1523 (1991).